


Dancing With Demons

by Enbies_Committing_Felonies



Category: Supernatural
Genre: Alternate Universe - Pirate, Angst with a Happy Ending, F/F, Gen, M/M, Pirate AU, Slow Burn, but i am apart of the fandom so..., dean adopts a cat because i say so, i do what i want and what i want is for everyone to be gay, i've never actually seen the show?, more tags will be added as we go along, sam and dean are pirates, there's a demon deal involved
Language: English
Status: In-Progress
Published: 2021-02-24
Updated: 2021-02-26
Packaged: 2021-03-14 21:20:41
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 2,605
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29673417
Author URL: https://archiveofourown.org/users/Enbies_Committing_Felonies/pseuds/Enbies_Committing_Felonies
Summary: Sam and Dean Winchester are known as the fiercest pirates to sail the ocean, but with tempers rising on the side of the law, the brothers have to be prepared to do anything to keep themselves afloat.To what lengths will the brothers go to in order to keep their business, and their crew, safe?What happens when they have to deal with a stow-away?
Relationships: Castiel & Sam Winchester, Castiel/Dean Winchester, Dean Winchester & Sam Winchester, Gabriel/Sam Winchester
Kudos: 2





	1. In Your Eyes I See a Fire That Burns

**Author's Note:**

> This was up on Wattpad, but the account I used to have I can't access anymore, so I decided to edit what I had posted so far and put it up on here. I hope you enjoy!!

Dean's forest green eyes glittered in the kerosene lamp's dim glow, and he yawned at the figure in front of him. "I don't care about the 'rules and regulations' crap as long as the deal is the same. Sam stays safe, I sell you my soul and die in ten years. Deal?"

The dark shadow shook it's head, "Due to the system and delicate specifics of this case, the agreement must be that you will die in three years instead of the original ten. Unless-" The roiling form that seemed to be made up of black soil and the velvet cloak of midnight, cut off the human's protests, "Unless you manage to freely give something of great value to you without expecting anything in return. Only then could you be free."

The demonic whirl gazed upon the man who dared risk so much for his kin. He had a smattering of freckles on his tanned face, and, though young and no more than twenty years of age, it was weather beaten. He had sandy brown hair and a rugged voice that sounded used to making hard bargains. His eyes shone brighter than polished silver in the moonlight even though the room was lit with only a flickering lamp. The demon found the man admirable, and almost felt wistful as the man surveyed its form without being able to meet its eyes.

"Good enough." The man finally replied. "I guess we need to seal the deal now?" He seemed a bit awkward, but not at all shy, and raised an eyebrow quizzically.

"Yes, a kiss is the customary tradition for such cases." It didn't understand the man's skepticism.

"Okay..." The man paused and gave what the demon could only assume was a pointed look.

"You have no body." Oh. That would explain it.

"I do not need a body, I have mass as this swirling shadow. If necessary, I could also take the shape of a human, such as you. Would you like to proceed, or do you wish to back out? It would be completely understandable."

The man shook his head, "No, we're doing this." He stepped forward and closed his eyes.

The kiss was over in a moment. Soft, delicate, and in any other circumstances could've been sweet. Dean backed away, and though he tried to hide it, the demon knew his hands were shaking.

"My work here is done. Good day, I'll be seeing you."

With that, the ball of smoke dissipated, leaving only a small, inky feather in it's place. Dean was alone again.


	2. Time is Racing Toward Us

**Summary for the Chapter:**

> The demon is assigned to ensure the retrieval of the soul

**Notes for the Chapter:**

> I'm doing this to get this fic out, not because I think it's good, but because I can't rest unless I finish it. Anyway, this one is short too <3

I finished my first deal.

I kissed someone.

I got someone's soul.

Of course, I had to give it to Crowley, the ruler of hell, but I still got it.

It was my first time.

I haven't been a demon for very long. Just one hundred sixty-nine years, one hundred ten of which were spent training and poring over rules. The other fifty-nine years were just waiting to get picked for an assignment, an endless game of 'older, more experienced demons get the gig'.

Before I was a demon... I think I was something powerful. But I must have died.

Sometimes I remember in snippets what my past was like, but normally my only clue is whispered conversations and fearful, side-long glances between spirits and demons.

Someday I'll find out what I was.

Oh Chuck. I kissed a man. I got a soul. I finally belong.

But it doesn't feel right. I guess I always knew it wouldn't, but I had hoped...

"Castiel, get in here!" It's Crowley, the commander of stolen souls. I approach him, changing into my human form as I got near him. He was a stickler for appearances.

"Yes sir?" His black eyes bore into mine.

"You gave this... Dean a three-year limit? Why?" I can't tell if he's angry or not.

"He had a very specific request. It was difficult to ensure the follow-through." I hope my response is adequate. I do not wish to be punished.

"The request was-?" His countenance gives me no clue as to what he is feeling.

"That his brother remain unharmed for the remainder of the unrest between the dark forces and the Royals, sir. I informed him that the limit was shortened due to the situation, unless he successfully completed task forty-two. That the seller give something of great sentimental value away without expecting anything in return." I stand at attention. Perhaps I did suitably.

All he does is pace.

Finally he pauses in front of me.

"You realize that in order to ensure that he either completes the requirements or fails, you must be present?"

"Yes. Uh, yes, Sir." My voice stumbles over my tongue, like a fumbling, newly-born puppy.

He gives a brisk nod, "Very well. Carry on. I will expect you to give reports."

"Yes sir."

A puff of smoke and he's gone, and I'm standing on a dock, men in uniforms and rags bustling about me, like a beehive.

I spot a nicely trimmed ship with the words _Wayward Impala_ painted neatly on her side. Winchester's.

I make my way towards it.

**Notes for the Chapter:**

> Chapter title is a line from "Make a Man Out of You" from Mulan


	3. You Don't Have to Promise Heaven or Paradise

**Summary for the Chapter:**

> Cas makes his place on the ship.

**Notes for the Chapter:**

> y'all still reading this?? because in a chapter or two it's going to start being newly written chapters. which might be better (but also might not if ya know what I mean)

I stumble my way up to the large boat, not used to the physical body I now inhabit.

"Come on, Sammy. Time to haul out!" I hear a voice yell. A muffled voice shouts in response, and I follow the sound up to where sailors are loading a few crates and barrels onto the deck, before bringing them into the hold below.

"C'mon, crew. We wanna leave before next week!" His voice is... crisper - sharper? - than when we were speaking below deck. Perhaps because this human body has actual hearing organs.

I make my way onto the boat, avoiding the sailors. It's easier than I expected and I decide to study the vessel.

The _Wayward Impala_ has a small crew for its size, but it seems to work efficiently. Dean is the captain, and his brother, Sam, must be the first mate. I wonder who else is aboard? As I stand on the deck of the boat, I notice that the men seem on edge. At least two men don't seem to be doing anything other than standing around, and keeping a lookout. And all the other sailors are constantly looking over their shoulders, and glancing about.

But they still don't see me. I relish in my body's sight organs, and roll them heartily. Human's are rather dumb.

I go back to studying the ship. It's solid, made of strong wood, and well-kept, with a spotless deck and paint job. The deck is neat, not overcrowded with barrels or anything else, and there is a sense of life throughout the entire crew, despite their nervous electricity. I pause for a moment, as the captain's voice rings out again.

"Alright, one last sweep of the ship before she sails! I want her ship-shape!"

There is a collective groan at his play on words, but the crew dutifully finishes up whatever they were doing and begin to search the deck and everywhere else. Oops. I should probably hide or something.

I manage to get belowdecks and hide in the first room I find that seems suitable. It is a beautiful room, in my opinion, with a window, surprisingly, and gauzy curtains. To the side is a bed, nailed to the floor, and to the other is a bookshelf with small 'fences' and latches to keep the books from falling out with the swaying of the boat. At the foot of the bed is a trunk, made of dark, smooth wood and brassy metal.

On the side with the books is a modest desk, and I make way towards it. A single sheet of paper lays discarded in the corner, and I pick it up, marveling at the intricacies of the muscles in my hands. Unfolding the crumpled letter, I begin to read.

_'Dear Sammy, I don't really know how to start this, and in all honesty I will likely throw it away, and re-write this over and over. I may never man-up enough to tell you, or I might just leave a letter for you to find when I am gone. But I'm not one for chick-flick moments, so I won't draw this out._

_I'm gonna die, Sam. I'm going to die in three years, because I wasn't gonna let you get hurt. And I wasn't gonna let my crew suffer. But you don't need to worry about me, I'll live out my last years like they're my best, and who knows? Maybe we'll finally hijack a king's ship._

_I guess I should explain though, the reason I'm dying. The truth is, I made a deal. A deal to keep you, and our crew safe, during the entire period of unrest what with the high-tops and dark forces fighting. But it wasn't a normal deal, Sam, it was a demon deal, so now I'm going to die._

_I love you Sammy, and when I'm gone you better make sure my ship is safe, or I swear I will haunt you forever._

_-Dean Winchester'_

I set the paper down, shaken. Is every man as willing and unafraid to give up himself to unknown forces for a brother? For a group of rowdy sailors? Or is Dean just an exceptional example of loyalty?

The clattering of the deck settles into a more calm intensity, and I decide now is the time to finish my hiding job. Tucking the paper into my pocket, I rummage through the trunk, snapping my fingers and creating a false pocket in the bottom by distorting reality enough to create an extra layer. Then I climb in.

I'm officially a stowaway.

**Notes for the Chapter:**

> Chapter title is a line from the song "Stowaway in Your Heart"


	4. Cat Got Your Tongue?

**Summary for the Chapter:**

> Dean finds himself growing fond of a cat after a prank is pulled on him.

**Notes for the Chapter:**

> I don't know why I wrote this chapter the way I did?? I'm pretty sure it was in the middle of the night or something. Anyways, enjoy as much as you want to of it.

With baby underway and the salty sea air winding through my lungs, I find it hard not to smile.

This. This is the life I've chosen. Brother beside me, crew working with me, my beautiful ship cleaving through the sea like a harpoon.

This is what I have given my life for.

Laughter comes from the port quarter, and I turn towards the pleasant sound.

"Ye better not be running a rig so soon outta berth, I've not the patience for it!" I call out, but I'm smiling, and whoever the young rascal is -I wager it's Gabriel, the new cook- likely hears the lack of threat in my voice.

"Aye captain, there'll be no shenanigans from me. Not on a week of Sundays, you can bet your bottom dollar on that sir!!"

It doesn't reassure me in the slightest, since when I initially asked him if he wanted to be part of the crew I had just caught him attempting to pickpocket me in his own tavern, the knave, but I decide to let it slide. This last haul of ours has me in a dandy mood, and I don't warrant what will probably be a harmless prank as a reason to ruin it.

Making my way amidship, I think of how Sammy will get on without me. As quartermaster he'll be hard-pressed to hold the crew together, not that he'll want to. But I hope to be successful enough that he can retire from this lifestyle if he wants. Make something of himself.

I go below, absently scrubbing a hand down my face. Sam deserves the truth. I pause before the door of my cabin, hand poised over the handle. Oughtn't I tell him? Do I dare? I turn the handle-

And jump back.

"Blimey! Who's the bilge-sucking reptile that left a damned puss-cat in my cabin?!"

A small multicolored kitten yawns up at me, pink mouth filled to the brim with pearly needle-like teeth. Its eyes a striking green against a mostly black body, with large gray patches, medium orange-y patches, and small white feet, and a noticeable white splotch over its left eye.

Gabriel materializes beside my right shoulder, hands stuck in his pockets and a pie-eating grin on his face. I resist the urge to deck him in his pretty little face before throwing him overboard. I wouldn't want to do that to the crew though, since he's the first decent cook we've had on board in over three months. We might be pirates by all accounts, and we'll never be royals by any means, but when each member of your crew loses at least ten pounds within a week from food poisoning, well, thats not very pleasant business. Plus he makes a mean pie.

"Was it you?" Any sane man would have taken my tone as dangerously calm, but the Cook just keeps grinning, using one hand to brush a strand of his golden hair to the side.

"Why, whatever makes ye think that, Captain?" His voice is one of complete innocence, but his eyes have the glint of a trickster.

"Well what in the name of the briny deep am I supposed to do with a Death's head on a mop stick such as that?!" I gesture at the kitten, who somberly blinks its eyes at me before lightly standing and winding its gaunt frame around my trouser leg, reaching up with its tiny feet and kneading at my leg.

"The hell?!" I can't have a cat on this ship, I'm allergic!

But... it was a _little_ cute. Only a little.

"You could use it as a rat catcher, Lord knows we need one. Have you seen our vittles? Why just the other night I was-"

"I don't care what you were doing!" I burst out, "What were you thinking??"

"I never said it were me, Captain." He winks, gives a mock salute, and vanishes down some hatch or somewhere. I don't really pay attention. My mind still on the underfed, scrappy, probably fly-ridden kitten at my feet. It blinks. I hang the jib at it. It blinks again.

"Well get on wit' it, will you?!" I grumble, gently pushing it into my room with my boot before gingerly stepping over it and closing the door. "What a nuisance." It doesn't reply. Jerk.

I settle on my bed and worry my bottom lip with my teeth, rolling my eyes when the kitten hops up beside me, butting its small head against my arm.

"I guess you wouldn't know how to tell yer brother that you're gonna die in three years, eh kit?" It buts its head against my arm again, its green eyes unblinking. I groan and push it away, but it only mewls and returns to my arm, pressing its skinny body between my chest and my arm and beginning to vibrate without warning.

"What the bloody-?!" I keep from jumping away from it. What is it...?

It keeps vibrating.

Cautiously I bring a hand and place it on its head. It mewls again and presses against me harder. It seems a bit young to be without a mother. Probably hungry, poor thing...

I grumble as I stand and cross over to my desk, the small body of the kit tucked in my arm. I pull open the drawer and draw out a small piece of bread. I don't even know why I had it in there.

"Here kit, how about some vittles?" Its unacceptable to just call it 'the kit'. I study its tiny face as I break apart the bread into manageable bites, and slip pieces to it. It tucks in ravenously. The eye with a white patch around it makes me think of pirates, and it's only fitting since it _is_ a pirate's cat...

"Calico Jack." I murmur to it. It glances up at me, then turns its attention back to the food.

"Calico Jack." I like it.

**Notes for the Chapter:**

> That was the last one I had to copy, so from here on out they'll all be written at the time they're posted (instead of literal years ago skjhdkahfksd)

**Author's Note:**

> Chapter title is a line from the song "Devil's Dance"  
> ~~  
> If you liked it, please comment!! it gives me motivation :)


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